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Resolution of 3-(methylamino)-1-(2-thienyl)propan-1-ol, a new key intermediate for duloxetine, with (S)-mandelic acid

✍ Scribed by Kenichi Sakai; Rumiko Sakurai; Atsushi Yuzawa; Yuka Kobayashi; Kazuhiko Saigo

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
229 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

The resolution of racemic 3-(methylamino)-1-(2-thienyl)propan-1-ol 3, a new key intermediate for duloxetine 1, was studied. The conditions were optimized for an industrial-scale resolution of 3 by using (S)-mandelic acid 4 as a resolving agent and 2-butanol containing 2 equimolar amounts of water as a solvent. The (S)-3•(S)-4•H 2 O diastereomeric salt was crystallized to give pure (S)-3 with >99.9% e.e. after liberation of the amine. The absolute configuration of liberated (-)-3 was determined as (S) by X-ray crystallography.

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